Error Sending

Installed on FC 4 and running/receiving messages fine. However, when a message is attempted to be sent an error is thrown (below). I know it is not the connection as I can telnet to that domains mx from the Zimbra machine on port 25 and talk fine with the other mail server.

The setting is the local host name (linhost.tmcentral.net) and the Zimbra smtp port is port 25. It appears to occur on any given remote smtp server (tested using exchange and mdaemon as the remote servers).

Originally Posted by anand

Looks like tomcat+javamail is waiting for a 250 after DATA command
and is not getting it? Are you making your "is sending 250/221" conclusions
from tcpdump?

No, I am making them from a remote server's log (to which I have access) of the smtp session between it and the Zimbra host box. I can also confirm that all tested remote servers accept the mail and send the 250/221 commands (and deliver the mail to their respective boxes). Any other ideas?

check postfix health next

Check /var/log/maillog (FYI: in the future we will have zimbra installed postfix log to /var/log/zimbra.log - log consolidation).

Looks to me like the postfix is unhappy for some reason and tomcat is timing out on postfix. There should be something useful in the postfix logs.

(PS: on a related note, did you set relay host in the zimbra admin console so postfix can relay to exchange? if you set in the admin console, we have a periodic script than scans LDAP and pushed postfix config, so after a certain delay you should see postfix pick up the change - the reason I bring this up is because postfix will wedge if it thinks mail loops to itself etc - because of a misconfiguration.)

It gets weirder...

Check /var/log/maillog (FYI: in the future we will have zimbra installed postfix log to /var/log/zimbra.log - log consolidation).

Here's a funny thing... I just tried to send again and it worked flawlessly! Not really sure whats going on since I didn't change anything! Nevertheless, I'm going to compare the postfix log you note with the zimbra.log and will post the results where it errored, just to understand what went wrong!

Originally Posted by anand

(PS: on a related note, did you set relay host in the zimbra admin console so postfix can relay to exchange? if you set in the admin console, we have a periodic script than scans LDAP and pushed postfix config, so after a certain delay you should see postfix pick up the change - the reason I bring this up is because postfix will wedge if it thinks mail loops to itself etc - because of a misconfiguration.)

I did not set any relaying/"Smart Host" up at all.; should I have? This is a lab with another server on the local subnet that has no issue sending (all RFC reqs are met for the IP) so I didn't see any need to have a backup relay for testing (after all, in testing my goal is to make sure the native process works; the email contents are garbage at this point anyway!)

Dns

Originally Posted by dmoring

I did not set any relaying/"Smart Host" up at all.; should I have? This is a lab with another server on the local subnet that has no issue sending (all RFC reqs are met for the IP) so I didn't see any need to have a backup relay for testing (after all, in testing my goal is to make sure the native process works; the email contents are garbage at this point anyway!)

You don't need a smart host, unless the DNS lookups from the ZCS server aren't working - if postfix can't find the next hop (which doesn't appear to have been the case) it won't send the message.

don't panic!

I had similar problems just as described and the logs were all similar, timeout and yeap it was the fact postfix wasn't happy.

In this case it was my fault - if you ever find yourself managing distribution lists and adding mailing list protections (which imvho should have been done via a gui) - and if you ever mess with the internal files as I did (there wasn't any other way anyhow) - as described here - RestrictPostfixRecipients - ZimbraWiki..

Don't..ever.. remove.. the .db and permitted senders list file on its own - you will have to retrace all your steps and remove all the referals to these files such as those in the script /opt/zimbra/postfix/conf/update_protected_recipients as well as in /opt/zimbra/postfix/conf/main.cf

Gave me quite a scare this morning as I know nothing about email servers nor how to troubleshoot them!